Historical clue formulations

• "Can't win 'em all" — 2023-12-31
• Comment of resignation applicable to 17-, 28- and 50-Across? — 2018-10-16
• Phrase of resignation — 2016-09-06
• "Win some, lose some" — 2011-05-31
• "Win some, lose some" — 2008-01-11
• 1966 Frank Sinatra hit — 2006-09-22
• "Oh, well" — 2004-09-18
• Utterance that sums up 20-, 32- and 42-Across — 2004-04-19